GB1502791A - Process for the conversion of niddamycin to leucomycin a1 to leucomycin a3 and 3-(o)-alkanoyl esters thereof and to carbomycin b and 3-(o)-alkanoyl esters thereof and provision of dimethyl acetals of said compounds - Google Patents
Process for the conversion of niddamycin to leucomycin a1 to leucomycin a3 and 3-(o)-alkanoyl esters thereof and to carbomycin b and 3-(o)-alkanoyl esters thereof and provision of dimethyl acetals of said compoundsInfo
- Publication number
- GB1502791A GB1502791A GB19950/75A GB1995075A GB1502791A GB 1502791 A GB1502791 A GB 1502791A GB 19950/75 A GB19950/75 A GB 19950/75A GB 1995075 A GB1995075 A GB 1995075A GB 1502791 A GB1502791 A GB 1502791A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkanoyl
- niddamycin
- leucomycin
- dimethyl acetal
- alkanoyl esters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- REPPNUPKOJKPSP-ZZNWINOMSA-N Niddamycin Chemical compound CO[C@H]1[C@H](O)CC(=O)O[C@H](C)C\C=C\C=C\C(=O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)C(C)C)[C@](C)(O)C2)[C@@H](C)O1 REPPNUPKOJKPSP-ZZNWINOMSA-N 0.000 title abstract 5
- IEMDOFXTVAPVLX-YWQHLDGFSA-N Leucomycin A1 Chemical compound CO[C@H]1[C@H](O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@@H](C)O1 IEMDOFXTVAPVLX-YWQHLDGFSA-N 0.000 title abstract 4
- IEMDOFXTVAPVLX-UHFFFAOYSA-N 15-oxo-cleroda-3,13E-dien-18-oic acid Natural products COC1C(O)CC(=O)OC(C)CC=CC=CC(O)C(C)CC(CC=O)C1OC1C(O)C(N(C)C)C(OC2OC(C)C(OC(=O)CC(C)C)C(C)(O)C2)C(C)O1 IEMDOFXTVAPVLX-UHFFFAOYSA-N 0.000 title abstract 3
- IEMDOFXTVAPVLX-ADNGMUMBSA-N Leucomycin-A1 Natural products CO[C@H]1[C@H](O)CC(=O)O[C@H](C)CC=CC=C[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]1O[C@H](C)[C@@H](O[C@H]2C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O2)[C@@H]([C@H]1O)N(C)C IEMDOFXTVAPVLX-ADNGMUMBSA-N 0.000 title abstract 3
- PXUIVECFRJIQIG-UHFFFAOYSA-N Niddamycin Natural products COC1C(CC(CC(C)C(=O)C=CC=C/CC(C)OC(=O)CC1OC(=O)C)C=O)OC2OC(C)C(OC3CC(C)(O)C(OC(=O)CC(C)C)C(C)O3)C(C2O)N(C)C PXUIVECFRJIQIG-UHFFFAOYSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 title abstract 2
- -1 dimethyl acetals Chemical class 0.000 title abstract 2
- 229930188120 Carbomycin Natural products 0.000 title 1
- FQVHOULQCKDUCY-OGHXVOSASA-N [(2s,3s,4r,6s)-6-[(2r,3s,4r,5r,6s)-6-[[(1s,3r,7r,8s,9s,10r,12r,14e,16s)-7-acetyloxy-8-methoxy-3,12-dimethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimeth Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@H]1[C@@H](CC=O)C[C@@H](C)C(=O)/C=C/[C@@H]2O[C@H]2C[C@@H](C)OC(=O)C[C@H]([C@@H]1OC)OC(C)=O)[C@H]1C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O1 FQVHOULQCKDUCY-OGHXVOSASA-N 0.000 title 1
- 229950005779 carbomycin Drugs 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 title 1
- XJSFLOJWULLJQS-NGVXBBESSA-N josamycin Chemical compound CO[C@H]1[C@H](OC(C)=O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@@H](C)O1 XJSFLOJWULLJQS-NGVXBBESSA-N 0.000 title 1
- 229960004144 josamycin Drugs 0.000 title 1
- XJSFLOJWULLJQS-UHFFFAOYSA-N leucomycin A3 Natural products COC1C(OC(C)=O)CC(=O)OC(C)CC=CC=CC(O)C(C)CC(CC=O)C1OC1C(O)C(N(C)C)C(OC2OC(C)C(OC(=O)CC(C)C)C(C)(O)C2)C(C)O1 XJSFLOJWULLJQS-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 abstract 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 6
- 230000003301 hydrolyzing effect Effects 0.000 abstract 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 150000001241 acetals Chemical class 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/476,016 US3970642A (en) | 1974-06-03 | 1974-06-03 | Process for the conversion of niddamycin to leucomycin A1, leucomycin A3, carbomycin B and other antibiotics and related 3-O-esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1502791A true GB1502791A (en) | 1978-03-01 |
Family
ID=23890150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19950/75A Expired GB1502791A (en) | 1974-06-03 | 1975-05-12 | Process for the conversion of niddamycin to leucomycin a1 to leucomycin a3 and 3-(o)-alkanoyl esters thereof and to carbomycin b and 3-(o)-alkanoyl esters thereof and provision of dimethyl acetals of said compounds |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3970642A (enExample) |
| JP (1) | JPS514189A (enExample) |
| CA (1) | CA1048019A (enExample) |
| FR (3) | FR2288749A1 (enExample) |
| GB (1) | GB1502791A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4851518A (en) * | 1985-12-23 | 1989-07-25 | Schering Corporation | Di and tri-O-acetyl-"O-iso-valeryl-23-O-demycinosyl tylosins, hydrazone derivatives thereof and processes for their preparation |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3792035A (en) * | 1970-05-04 | 1974-02-12 | Meiji Seika Kaisha | Mono-acetyl derivatives of antibiotic sf-837 and sf-837-a2 substances and production thereof |
| US3784447A (en) * | 1972-04-17 | 1974-01-08 | Abbott Lab | Mycarosyl macrolide antibiotics |
| DE2361059A1 (de) * | 1973-12-07 | 1975-07-24 | Hoechst Ag | Verfahren zur herstellung von (androst-17 beta-yl)-alpha-pyronen |
-
1974
- 1974-06-03 US US05/476,016 patent/US3970642A/en not_active Expired - Lifetime
-
1975
- 1975-05-12 GB GB19950/75A patent/GB1502791A/en not_active Expired
- 1975-06-02 JP JP50065458A patent/JPS514189A/ja active Pending
- 1975-06-02 CA CA228,236A patent/CA1048019A/en not_active Expired
- 1975-06-03 FR FR7517321A patent/FR2288749A1/fr active Granted
-
1976
- 1976-01-22 FR FR7601711A patent/FR2288106A1/fr active Granted
- 1976-01-22 FR FR7601712A patent/FR2288107A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS514189A (enExample) | 1976-01-14 |
| FR2288749A1 (fr) | 1976-05-21 |
| CA1048019A (en) | 1979-02-06 |
| FR2288106A1 (fr) | 1976-05-14 |
| FR2288749B1 (enExample) | 1979-07-20 |
| FR2288107A1 (fr) | 1976-05-14 |
| US3970642A (en) | 1976-07-20 |
| FR2288107B1 (enExample) | 1980-02-22 |
| FR2288106B1 (enExample) | 1979-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |